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This $600,000 Lesson Proves You Can’t Outsource Your Filing Deadline

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Wayne Lee, a Florida surgeon, hired CPA Kevin Walsh to prepare and file his tax returns. From 2014 through 2016, Wayne provided Kevin with all necessary documents and signed Form 8879 e-file authorizations each year. As far as Wayne knew, Kevin was doing exactly what he’d been hired to do: preparing and filing returns, each showing mid-six-figure tax liabilities but also substantial refunds due.

Wayne discovered the truth on December 5, 2018, when an IRS agent showed up at his office. Kevin had never filed any of those returns. He’d never told Wayne about a software issue that supposedly prevented e-filing. The IRS notices had piled up at an incorrect address that Kevin promised but failed to update. By the time Wayne discovered the problem, the three-year statute of limitations had expired on his $288,000 refund from 2014. Instead of rolling that refund forward as planned, Wayne ended up paying $289,000 to the IRS in 2019 to settle unpaid liabilities, penalties, and interest.

Wayne sued Kevin (settling out of court) and the federal government for a refund. The government won.

In a recent episode of Tax in Action, host Jeremy Wells, CPA, EA, uses Wayne’s case to explore a principle the Supreme Court established decades ago: you can delegate tax return preparation, but you can’t delegate responsibility for filing deadlines. Understanding this distinction and the penalties that follow when taxpayers miss deadlines is crucial for tax professionals and their clients.

How Failure to File and Failure to Pay Penalties Work

The penalties Wayne faced were calculated additions to tax that accrued interest and turned a potentially manageable balance into a serious financial burden.

The failure to file penalty under IRC Section 6651(a)(1) is the more severe of the two delinquency penalties. It’s 5% of the net amount due for each month or fraction of a month the return is late. That “fraction of a month” language carries real weight. File your return one day late, and you owe a full month’s penalty. The penalty maxes out at 25% of the net amount due, unless fraud is involved. In fraud cases, the penalty jumps to 15% per month with a 75% ceiling.

“The net amount due means the tax liability shown on the return less any withholding credits, estimated payments, or any other payments made on or before the due date,” Wells explains, emphasizing a critical point. This definition, from IRC Section 6651(b)(1), means even if you can’t file on time, making payments  reduces the base amount for penalty calculations.

The failure to pay penalty under IRC Section 6651(a)(2) is gentler at 0.5% per month, but it comes with its own trap. As Wells explains, “An extension of time to file is never an extension of time to pay.” Treasury Regulation 1.6081-4(c) makes this explicit. That six-month extension gives you time to finish the paperwork, not time to find the money.

When both penalties apply, as in the case of an unfiled return with an unpaid balance, they don’t stack. The failure to file penalty gets reduced by the failure to pay amount, keeping the combined rate at 5% per month. But both count as “additions to tax,” meaning interest accrues on the penalties themselves, compounding the total amount owed over time.

The math drives the strategy. As Wells puts it, “Why pay 5% when you only have to pay 0.5%?” Always file on time, even with a balance due. Always request extensions if you need more preparation time. And make estimated payments before April 15th to reduce the net amount due that serves as the penalty base.

Partnerships and S Corporations Face Different Rules

Pass-through entities don’t pay income tax directly, so there’s no failure to pay penalty. But their failure to file penalties can be devastating.

Under IRC Sections 6698 (partnerships) and 6699 (S corporations), the penalty is an inflation-indexed amount per partner or shareholder, per month the return is late. For 2025, that’s $245 per partner or shareholder, increasing to $255 in 2026 and $260 in 2027.

Wells stresses the multiplication effect. “By definition, a partnership has at least two partners. So if you have a late 1065, then at a minimum, the penalty will be doubled.” A small partnership with four partners and a three-month late filing would owe nearly $3,000 in penalties for 2025.

The penalty amount is determined by the year the return should be filed, not the tax year of the return. So if you file a 2024 partnership return late in 2025, you use the 2025 penalty amount.

Relying on Your Tax Professional Won’t Save You

Wayne’s defense seemed reasonable. He hired a licensed CPA, signed e-file authorizations, provided all documents, and was repeatedly assured his returns were being handled. Surely that demonstrates ordinary business care?

The courts said no, following precedent from United States v. Boyle (1985). In that case, the Supreme Court reversed an appeals court that sided with a taxpayer whose attorney missed an estate tax filing deadline. The Supreme Court held that taxpayers cannot delegate filing and payment deadlines to professionals.

When Wayne’s case reached the 11th Circuit in 2023, his attorneys argued that e-filing changes this dynamic. If only the professional can electronically submit returns, doesn’t that shift responsibility? The court rejected this argument entirely. “E-filing does not change the taxpayer’s duty,” they ruled.

So what actually qualifies as reasonable cause? The IRS outlines acceptable categories in Internal Revenue Manual 20.1.1.3.2:

  • Death or serious illness of the taxpayer, immediate family member, or key employee within an organization (not an outside professional)
  • Fire, casualty, or natural disaster directly causing non-compliance
  • Legitimate inability to obtain essential records after reasonable efforts (poor recordkeeping doesn’t count)
  • Reliance on erroneous written IRS advice specifically addressing your situation
  • Ignorance of the law, but only if you had no prior filing requirement, tried to learn the law, and the issue was genuinely complex

Wells notes a crucial limitation: if you’re “demonstrably competent enough to carry on other transactions,” like hiring and working with a tax professional, “reasonable cause won’t work.”

The message is clear: tax professionals can prepare returns and provide advice, but the legal duty to ensure filing and payment remains with the taxpayer.

First-Time Abatement Is Your Best Shot at Relief

While reasonable cause rarely succeeds, taxpayers have another option that’s often more accessible: First-Time Abatement (FTA).

The IRS evaluates penalty relief requests in a specific order, outlined in IRM Chapter 20:

  1. Correction of IRS error
  2. Statutory and regulatory exceptions
  3. Administrative waivers (including FTA)
  4. Reasonable cause

Notice that FTA comes before reasonable cause, even though reasonable cause is statutory. The National Taxpayer Advocate has criticized this ordering, but for taxpayers, it creates opportunity.

FTA covers failure to file, failure to pay, and failure to deposit penalties, but not the underpayment penalty. To qualify, you need:

  • Clean penalty history for three prior years (no unreversed penalties)
  • All required returns filed
  • Tax paid or payment arrangement in place

A critical change occurred in March 2023. “If you have a taxpayer with a relatively small penalty and you don’t ask for first time abatement, and then the following year they get an even bigger penalty, first time abatement is not available because it should have been used on that first penalty,” Wells explains. 

The old strategy of “saving” FTA for a potentially larger future penalty no longer works. Use it when you’re eligible, or lose it.

Timing matters for requesting FTA. You can’t abate a penalty before it’s assessed, so wait for the notice—typically a CP14 or CP162. Get Form 8821 or 2848 authorization from clients and check the box to have notices forwarded to your office. When the notice arrives, respond immediately or call the Practitioner Priority Service for faster resolution.

Good news is coming: the National Taxpayer Advocate announced that starting with tax year 2025 returns, the IRS will begin automatically applying FTA to eligible penalties. Until then, it remains a manual process.

Protecting Yourself and Your Clients

“Penalty abatement is really less about proving innocence and more about understanding the timing, the procedures and how the IRS operates,” Wells says to summarize the episode’s overarching message. 

For tax professionals, this means building clear communication into every client engagement. Clients must understand that while you prepare returns, they’re still responsible for confirming filing and payment. This isn’t about avoiding responsibility; it’s about accurately representing how tax law works.

Wayne Lee did everything a reasonable person would do, yet still lost nearly $600,000. His case is a reminder that in tax compliance, good intentions and professional help aren’t enough. The responsibility to file and pay on time ultimately rests with the taxpayer, and they can’t delegate that duty.

Listen to the full episode of Tax in Action for Jeremy’s’ complete analysis of IRC Section 6651, including detailed penalty calculations and step-by-step guidance for requesting abatement.

Why Your Audit Fails Before Fieldwork Even Starts

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“Some audits are doomed before the fieldwork even begins.”

In Episode 2 of Audit Smarter, Sam Mansour cuts to the heart of a problem many audit professionals face but don’t fully understand. You’ve been there: an experienced team, solid procedures, and a reasonable budget. Yet somehow, the engagement still feels like constantly playing catch-up. Testing seems disconnected. Risks surface at the worst possible moment. Partners ask questions during review that should have been answered weeks ago.

The culprit? Poor risk assessment that undermines everything that follows.

Most audit professionals understand risk assessment is important, but few realize how dramatically it shapes their engagement. Mansour explains, “The risk assessment drives the entire audit approach. And if we misidentify or overlook specific audit risks, your testing could be misaligned, and you could waste time. But even more concerning, you might miss material misstatements.”

Here’s what’s happening across the profession and, more importantly, what you can do about it.

Why Risk Assessment Gets the Short End of the Stick

The problem isn’t that auditors don’t know how to assess risk. It’s that firms have systematically devalued this critical phase, treating it as administrative overhead rather than the strategic foundation it actually is.

“Many teams view planning just as a compliance step and not as a strategic one,” Mansour observes. Budget pressures and efficiency demands create an environment where teams feel pushed to rush through risk assessment. “We devalue the risk assessment phase. We think of it as a textbook thing. Let’s just check some boxes and move on.”

This leads to what Mansour calls “pencil whipping,” mechanically completing checklists without genuine thought or analysis. The evidence shows up everywhere in audit files: work paper references that don’t make sense, incorrect years, or references to people who no longer work at the organization.

“It’s pretty clear it’s been rolled forward,” Mansour notes. “And it’s also very clear no one read through it.”

When external reviewers, whether peer reviewers or regulators, see this kind of documentation, it immediately raises red flags. “As a peer reviewer, you look at some of these risk assessments, and it’s crystal clear they just rolled this from last year and they didn’t even look at it,” he explains. “You’re probably going to be pretty strict when you’re looking at the rest of that file because clearly these guys are just rolling from the prior year.”

The pressure to be “efficient” in planning creates a dangerous cycle where the foundation of the audit becomes weaker, making it much harder to execute proper testing throughout the engagement.

5 Common Mistakes That Derail Audits

Understanding where things typically go wrong helps you avoid these pitfalls in your own engagements. Mansour identifies several patterns that consistently create problems.

Generic, Template-Driven Approaches

When risk assessments are generic and not customized to the specific client, the walkthroughs and procedures that follow suffer. “If we are general or vague in our identification of risks, it results in generic audit procedures,” Mansour explains.

Copying Prior Year Without Thinking

Using prior-year documentation as a starting point makes sense, but many teams go too far. They simply copy everything over with minor adjustments, becoming “a little complacent, a little lazy” in the rollover process. A better approach is to use prior-year information as a guide but take a fresh perspective on the current year.

Failing to Link Risks to Procedures

One “gut-wrenching” moment in an audit review happens when the audit team identifies risks in checklists, but no corresponding procedures address them. “You identified this risk, but what did you do about it?” This mistake exposes fundamental gaps in audit logic.

Superficial Inquiries

Take related party transactions, for example. Many auditors accept a simple “we have none” from the client and move on. But as Mansour points out, “that’s not sufficient.” Instead, “auditors should dig into board minutes, vendor relationships, and ownership records” to understand whether related parties exist and what transactions might occur.

Misusing Junior Staff

Sending inexperienced team members to conduct walkthroughs without proper guidance is a recipe for problems. Junior staff might identify three issues out of ten while missing critical problems that experienced auditors would catch immediately. “Sometimes you need experience to tell you, you’re looking at ten different things and eight of them are going to be a problem and two of them are not,” Mansour explains.

The solution isn’t to avoid using junior staff. It’s to pair them with experienced team members who can provide real-time guidance and fill in the gaps.

Practical Tools to Strengthen Your Risk Assessment

The good news is that these problems are entirely fixable with the right approach and tools. Here’s what works:

  • Dynamic checklists. Move beyond simple checkbox exercises to checklists that challenge teams to collect new information and think deeply about what they find. Ask different types of questions that force auditors to go beyond surface-level inquiries.
  • Structured brainstorming sessions. Don’t just conduct one brainstorming session and call it done. Mansour recommends peppering collaborative discussions throughout the engagement. “Have the engagement team go out to lunch and consider that part of your brainstorming activity,” he suggests. These sessions force teams to share knowledge and often uncover overlooked areas.
  • Early data analytics. Instead of treating analytics as nice-to-have add-ons, deploy them “immediately after engagement acceptance,” Mansour advises. His approach: “Give me your trial balance, and I will do some data analytics on it right from the get-go.” This generates specific issues to investigate before client meetings, allowing you to connect numbers to client stories strategically.
  • Simple intelligence gathering. Something as basic as Googling your client’s name can reveal critical information, yet “a lot of auditors won’t even do that,” Mansour observes. “You’d be shocked at some of the stuff” these searches uncover. Review prior audit findings, look for industry changes, and stay current on client updates.
  • Collaborative team approach. Instead of having one person update risk assessment documentation alone, assign different sections to different team members. This ensures multiple people read through and think about the content, rather than having it all flow through one person who might miss important details.

What Separates Top Performers

Firms that consistently execute superior risk assessments share several key characteristics that set them apart.

They Treat Risk Assessment as a Mindset

“Top performers treat risk assessment as a mindset, not just a task,” Mansour explains. “They understand that there’s value in risk assessments. It’s not just a checkbox on their list.” Their teams are intellectually curious rather than robotic, but this requires giving people adequate time and breathing room to think deeply.

They Create Collaborative Environments

These firms don’t silo team members into individual sections. Instead, they “connect the dots between client goals, internal controls, and audit processes with purpose.” Team members actively consider how discoveries in one area impact testing in others, creating a comprehensive understanding that reduces risk while improving efficiency.

They Invest in Proper Mentorship

Rather than throwing junior staff into complex situations alone, top performers create systematic mentorship structures. They pair junior staff with experienced seniors who provide real-time guidance, immediate field discussions, and progressive responsibility increases.

They Focus on Custom Solutions

Elite performers avoid generic approaches entirely. They tailor audit plans to each client and engagement year. Their team members can explain their logic clearly without defaulting to “it’s what we were told” or “it’s what we did last year.”

Three Changes to Make Right Now

If your firm wants to improve immediately, Mansour recommends focusing on these three foundational changes:

  1. Slow down in the planning process and allow for deeper team discussions. Invest upfront time that prevents downstream scrambling and quality issues.
  2. Ensure walkthroughs include a formal evaluation of control effectiveness with documentation customized to the specific client and current year rather than generic templates.
  3. Critically assess each risk and match it to custom procedures designed to address it, eliminating the disconnect between identified risks and actual testing approaches.

How You Know You Got It Right

Success in risk assessment is measurable through specific indicators. Your audit plan should be tailored, not generic. This demonstrates genuine client-specific thinking rather than template dependency. Your team members should be able to explain their logic clearly and provide substantive reasoning for their approaches.

Most importantly, when partners or regulators review your documentation, they should be able to “read your risk assessment and understand the rationale,” as Mansour puts it. They should see a clear narrative and strategic thinking rather than dry, templated responses.

If your team can’t explain their logic, or if external reviewers see obvious evidence of rolling forward prior year templates, you’re still in checkbox mode rather than strategic thinking mode.

The Foundation Makes the Difference

Risk assessment isn’t preliminary work that happens before the “real” audit begins. It’s the foundation that determines whether your entire engagement succeeds or struggles. As Mansour explains using a gardening analogy, if the risk assessment seed “doesn’t get planted properly, if it’s not cared for properly, it sets you up for failure.”

Firms that recognize this and invest accordingly create sustainable competitive advantages through systematically superior approaches to this critical phase.

The strategies and tools we’ve covered are proven approaches to transform your risk assessment process from liability into a strategic advantage. However, implementation requires commitment to changing how your firm approaches and uses its resources for this foundational work.

Ready to dive deeper into these risk assessment strategies and discover the specific frameworks top performers use? Listen to the full episode of Audit Smarter for Sam Mansour’s complete insights on transforming your approach to risk assessment and elevating your audit practice.